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You Will Need
Medium Oven-Safe Pan
Prepare the Ingredients
Preheat oven to 400 degrees. Prepare a baking sheet with foil. Set butter out to soften. Thoroughly rinse produce and pat dry. Trim ends of fennel bulb, quarter lengthwise. Use the tip of your knife to cut along the line where the tough core meets the rest of the fennel bulb on each section. Cut into ¼" slices. Stem kale and coarsely chop. Halve tomatoes. Combine parmesan cheese and panko in small bowl and stir together. Rinse steak, pat dry, and season with a large pinch of salt and pepper.
Roast the Garlic
Place garlic on a piece of foil, at least 6" by 6". Pour ¼ tsp. olive oil over garlic and season with a small pinch of salt. Bring foil corners together and scrunch to form a pouch. Place pouch on prepared baking sheet and bake in oven until garlic is soft, about 12-15 minutes. Remove from oven and allow to cool down. Reserve baking sheet for future step. Smash roasted garlic with the side of a knife or just mince it. In a small bowl, stir together smashed garlic, softened butter, and a pinch of salt and pepper. Set aside.
Make the Fennel Gratin
Place a medium oven-safe pan over medium heat and melt 1 Tbsp. butter. Add fennel and ¼ tsp. salt and stir together. Cover and cook 3-5 minutes, until fennel begins to get tender and caramelizes slightly. Remove cover, add evaporated milk and increase heat to high. Bring to a boil then remove from heat. If your pan isn't oven-safe, transfer fennel and cream to a casserole dish prepared with cooking spray. Sprinkle top with parmesan-panko mixture and place pan on top rack of oven. Bake 7-10 minutes, until the top is golden brown. Set aside.
Cook the Steaks
Place a medium pan over medium-high heat and add 2 tsp. olive oil. Add steaks to pan and sear until browned, about 3 minutes. Flip and repeat process. Remove steaks from pan and place on previously used baking sheet. Reserve pan for next step: no need to wipe clean. Roast steaks in oven until they reach a minimum internal temperature of 145 degrees, about 5 minutes, then remove from oven. Rest steaks at least 5 minutes.
Cook the Kale and Tomatoes
Return pan from previous step to medium-high heat. Add kale to pan, stir, and cook 2-3 minutes. Kale will crowd the pan at first but will wilt quickly. Add tomatoes, season with a pinch of salt and pepper, and cook for an additional 3 minutes, until kale is wilted and tomatoes are slightly softened. Remove from heat.
Plate the Dish
Place half of fennel gratin on each plate. Divide kale and tomatoes between both plates. Lean steak against kale and place half of the butter on each steak.